


Definitely Doing That Again

by justanotherbusyfangirl



Series: Dean and Donna's Sexy Experimentation [2]
Category: Supernatural
Genre: Bisexual Dean Winchester, Bottom Dean Winchester, F/M, Pegging
Language: English
Status: Completed
Published: 2017-09-06
Updated: 2017-09-06
Packaged: 2019-09-13 01:22:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16882941
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: Donna comes up with another kinky thing to do in the bedroom, expecting Dean to say no. She’s pleasantly surprised when he’s just as excited about it as she is.





	Definitely Doing That Again

It had been a while, years even, since Dean had done something like this.  It’s not that he didn’t like it anymore, he just hadn’t really had an opportunity with how busy life had gotten and how he wasn’t able to escape for a weekend anymore…

And then he and Donna had started their thing, becoming exclusive nearly a year ago, and that was that. No more of this, at least while he was with Donna, or so he thought.

Until she brought up the idea as another way to spice up their sex lives.  

The first thing they’d tried in the bedroom was blindfolds, Dean putting all of his trust into Donna’s hands.  After that, they’d branched out a bit, each coming up with ideas periodically and bringing them to the bedroom.  It was awesome, in Dean’s opinion, that he had found a girl who was willing to try things with him, but also understood when he was unsure.

When Donna had brought  _this_ up, though, she’d expected hesitation from Dean.  She never saw his enthusiasm coming.

That’s how Donna found herself kneeling at the foot of their bed, eyes trained on Dean’s lube-slicked fingers as they prepared his hole.  They’d both decided that he should prep himself, having experience doing so, at least the first time they did this.  If they decided to try it again, Donna would know what to do and could prep Dean, based on what she learned tonight.

Her eyes fell from between Dean’s legs to her own hips, the black dildo strap-on standing straight and proud from where she wore it.  It wasn’t terribly big, but they’d ordered multiple sizes for Dean to choose from, bigger ones that he could work up to later, if he wanted.

Donna was dripping already with the thought of what was about to happen.

Her eyes moved back up Dean’s body, heart pounding at the sight of Dean’s hand holding his knee up so that his legs were spread.  He had a look on his face that was a mixture of concentration and pleasure, and Donna couldn’t wait to see what he looked like when she began fucking him.

Her hand fell to the cock she was wearing, lube-slicked and ready for when Dean was.  She squeezed it, feeling the slight give it had in her hand. Moving it around slightly, she felt the underside press onto her clit, knowing that when she began to move inside of Dean she’d be feeling just as much pleasure as him.

“Donna…” Dean groaned, drawing her eyes back to his face.  He bit his lip as he held three fingers deep inside himself.  “I’m ready for you, baby.”

Donna whimpered at Dean’s words, eager to begin.  She leaned over his body to kiss him, feeling the dildo pressing against his thigh as she did so.  Their bodies were both humming with anticipation and neither of them wanted to hurt the other because of over eagerness, so they used the kiss to help ground themselves before Donna sat back again.

Dean’s fingers left his hole, hand moving to hold his other knee high and away.  The sight he made as he spread himself open for her had Donna’s body thrumming with lust, from his heated gaze and his legs spread wide to his leaking, purple cock and gaping hole.

Slowly, Donna lined up the dildo with Dean’s hole, checking one more time that it was slick enough. The last thing she wanted to do was hurt Dean in any way, so it was better to check for the hundredth time.

Happy with the lubrication, she pressed the head against his rim, notching it there before looking up at him.  

“Come on, Donna, don’t be nervous.  I want this,” Dean encouraged, saying exactly what she needed to hear before she pressed inside.  She kept her hips as steady as possible, the wider head of the dildo slipping inside of his body with a pop.

Dean’s eyes scrunched shut, feeling the way the head stretched him differently than his own fingers had.  “Dean?” Donna questioned, wanting to make sure he was okay before she continued.

Dean took a deep breath in and released it, his body relaxing as he did so.  His face relaxed as well and he opened his eyes to nod. Donna pressed forward again, sliding easily inside of him as Dean’s body pulled her into him.

“Oh, fuck…” Dean groaned, his hands on his knees spreading his legs even wider, sliding Donna inside of him quicker than she meant to.  “Yes!” Dean hissed as she bottomed out, the pressure of the strap-on on her clit perfect.

“Dean,” she moaned, staying still to let him adjust.  Carefully she leaned down, catching his mouth with hers again.  He kissed her back like a starving man, needing to feel her in every way possible as he was filled inside.  Their kiss broke off when Dean spoke.

“Need you to move, Don,” he whispered against her lips.  “Need you to fuck me.”

Donna nodded, wide eyed, and sat back again.  She braced her hands on Dean’s thighs, using them as leverage to ease her dick almost completely out of him, only keeping the head inside.  She took a deep breath, then thrusted forward once again, pressure strong on her clit.

Donna began a slow pace, getting used to having sex in this way.  It was exhilarating, being the one penetrating her partner, something she’d never experienced before.  She was loving the feeling of power as she looked down at Dean, spread out beneath her and looking wrecked already.

She sped up slightly, needing more friction on her clit as the ball of pressure built in her lower belly. Dean seemed to need it as well, his hips starting to rock to meet hers with every thrust.  

Carefully, Donna let go of one of Dean’s legs to wrap her hand around his cock, which was leaking terribly onto his stomach.  The touch of her fingers on him had him yelping, the added pleasure making his hole clench tighter.

Donna shifted, getting her feet underneath her at a slightly different angle and pressed in again, Dean’s eyes widening as he gasped.

“What?” Donna immediately froze, afraid she’d hurt him.

“Oh my God, Donna, please keep that angle, right there…fuck,” Dean groaned, throwing his head back. She slowly pressed in again, seeing the exact second when she hit Dean’s prostate.  “Right there, baby, please…” Dean pleaded, fingers grasping at his legs harder than before.

Donna bit her lip in concentration, trying to ignore the pleasure building inside of her so that she could give Dean what he needed first.  She kept her angle the same, hitting his prostate with every thrust as her hand pumped his cock in time.  

Dean was a quivering mess, crying out a mixture of her name and profanities as she fucked into him. She could tell he would be coming soon, so she sped up her thrusts and hand.  

“Yes, yes, yes, yes,” Dean began to chant, his eyes squeezed shut and his breathing hitched.  “So close, Don,” he whined as she twisted her hand on his dick one final time, pressing deep inside of him.

White spurts of come coated Dean’s chest as she worked him through his orgasm, ignoring her own pleasure to make sure he was worked completely through his high.  She slowed her movements, not wanting to overstimulate him, and let go of his softening cock.  He sighed in contentment before she finally pulled her strap-on out of his body, eyes mesmerized by the fluttering of his hole when it was empty.

Donna took a moment to unclasp the strap-on, letting it fall off one side of the bed.  Dean was dazed, the look on his face adorable as he came back to reality.  After a moment he reached for her, pulling her body to his.  

“You didn’t come,” he realized, both of them knowing that it was possible the strap-on wouldn’t completely push Donna over the edge.

“It’s okay,” she tried to say, happy enough that Dean had enjoyed their play, but he was having none of that.

“I’m too spent to move, but come here,” he insisted, pulling Donna up to straddle his face.  While his body was stretching out after being curled in on itself for the last half hour at least and too tired to do more work, he knew his tongue would do the just the trick.  

Dean held Donna’s hips down as her pussy smothered his face, his tongue and lips finding her clit immediately.  With the build up that she’d gotten from fucking Dean, she was screaming his name in no time, hands gripping the headboard as she coated his face in her release.  

Dean was grinning like the cat who got the canary when she moved away, chuckling at his expression. “You’re too good at that, Winchester,” she teased, curling up against his body.  

“You love it,” Dean retorted, wiping his face off before pulling her in for a kiss.  Donna melted into the kiss, hand finding the towel beside her and using it to clean Dean’s chest as best she could.

The kiss ended, Dean muttering a, “Thanks,” as the towel was tossed away before they crawled underneath the covers, bodies sated and happy.

“Definitely doing that again,” Dean mumbled into Donna’s hair, making her smile.

“Anything for you, Dean,” she replied, truth seeping through her words.  She knew she would do truly anything for the man she loved, and he the same for her.


End file.
